CN117295802A - Liquid crystal medium and electronic component - Google Patents
Liquid crystal medium and electronic component Download PDFInfo
- Publication number
- CN117295802A CN117295802A CN202280034363.XA CN202280034363A CN117295802A CN 117295802 A CN117295802 A CN 117295802A CN 202280034363 A CN202280034363 A CN 202280034363A CN 117295802 A CN117295802 A CN 117295802A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 209
- 238000001228 spectrum Methods 0.000 claims abstract description 10
- -1 cyclohexane-1, 4-diyl Chemical group 0.000 claims description 89
- 230000003287 optical effect Effects 0.000 claims description 51
- 125000004429 atom Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000004378 air conditioning Methods 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 238000005516 engineering process Methods 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 4
- NSUDGNLOXMLAEB-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid Chemical group OC(=O)CCCCOC1=CC=CC(O)=C1C=O NSUDGNLOXMLAEB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000014509 gene expression Effects 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000010287 polarization Effects 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000001902 propagating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 22
- 239000000463 material Substances 0.000 description 15
- 230000004044 response Effects 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- 239000004990 Smectic liquid crystal Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 208000011823 Juvenile amyotrophic lateral sclerosis Diseases 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000005670 electromagnetic radiation Effects 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000006193 alkinyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000004424 eye movement Effects 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- XFMBDDKBMWOUIZ-UHFFFAOYSA-N 1,3,5-trimethylidenecyclohexane Chemical compound C=C1CC(=C)CC(=C)C1 XFMBDDKBMWOUIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N 1,4-dimethylcyclohexane Chemical group CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 101100208473 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lcm-2 gene Proteins 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000208 hepatic perisinusoidal cell Anatomy 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/13363—Birefringent elements, e.g. for optical compensation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
- C09K2019/183—Ph-Ph-C≡C-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3009—Cy-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3025—Cy-Ph-Ph-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
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Abstract
The invention relates to a liquid-crystalline medium comprising a) one or more compounds of the formula I and one or more compounds of the formula T and one or more compounds of the formula S1,
Description
The present invention relates to Liquid Crystal (LC) media and electronic components comprising such LC media, which are operable in the Visible (VIS), infrared (IR) or microwave regions of the electromagnetic spectrum. The invention further relates to the use of the LC medium in the IR, VIS or microwave region and to a device comprising the electronic component.
Liquid crystal media have been used for many years in electro-optic displays (liquid crystal displays: LCDs) to display information by amplitude modulation of polarized light in the visible region, and are widely used in TVs, monitors or displays of portable devices such as tablet PCs, mobile phones, and the like.
Nematic liquid crystals have also been proposed for phase modulation of light: articles McManamon PF, dorschner TA, corkum DL, friedman LJ, hobbs DS, holz M, berman S, nguyen HQ, resler DP, sharp RC, watson ea.optical phase array technology proc ieee.1996;84:268-298.Doi:10.1109/5.482231 describes liquid crystal-based optical phased arrays for various types of sensor applications; the article Scott r.davis, george Farca, scott d.romimel, seth Johnson, michael h.anderson, "Liquid crystal waveguides: new devices enabled by > 1000waves of optical phase control," proc..spie 7618,Emerging Liquid Crystal Technologies V,76180E (month 2, 12 days 2010); doi 10.1117/12.851788 describes refractive beam steering using a waveguide structure.
Liquid crystal on silicon (LCoS) is a miniaturized reflective active matrix liquid crystal display or "microdisplay" that uses a liquid crystal layer on a silicon backplane. Which is also referred to as a Spatial Light Modulator (SLM).
The silicon back plane is an array of pixels each having a mirrored surface that can simultaneously act as an electrical conductor. Each pixel comprises a fixed mirror covered by an active liquid crystal layer having a twisted nematic alignment which can be switched to a homeotropic alignment by applying a voltage. LCoS microdisplays are small, typically less than 1.0 inch diagonal, but can achieve high resolution of 1/4VGA (7.8 ten thousand pixels) to uxga+ (over 200 ten thousand pixels).
LCoS displays also have very small cell thicknesses, typically about 1 micron, due to the small pixel size. When the device is operated in reflective mode, a low cell thickness is also required for light to travel twice through the LC layer. Thus, the liquid crystal phase used for these displays must have a high optical anisotropy Δn in particular, in contrast to the low Δn LC phase typically required for conventional reflective LC displays. The use of a small box thickness is preferred, especially for applications requiring a short response time, since the response time is proportional to the box thickness, typically decreasing twice.
Liquid crystal compounds with high birefringence often have an intrinsic smectic phase or induce the formation of smectic phases when mixed with other liquid crystal compounds, which has an adverse effect on the low temperature stability of the display.
LCoS was originally developed for projection televisions, but is also used today for wavelength selective switching, structured illumination, near-eye displays, and optical pulse shaping. The computer-generated hologram may be encoded on a spatial light modulator arranged to modulate the amplitude and/or phase of incident light forming part of a holographic projector as described in WO2020/015933 A1. Such projectors have been applied in heads-up displays (HUDs) and head-mounted displays (HMDs) that include near-eye devices.
Another application using liquid crystal based devices is light detection and ranging (lidar) -a method for measuring distance by illuminating a target with laser light and measuring reflection with a sensor. The difference in laser return time and wavelength can then be used to form a digital 3-D representation of the target. In WO2019/24052A1, a holographic LIDAR system using e.g. an LCoS SLM is proposed.
One of the most important characteristics of a phase-only LCoS device is its use of an optically nonlinear liquid crystal material that is sensitive to operating temperature. While LCoS devices have in the past focused primarily on optical intensity modulation that is rarely affected by temperature changes, for phase-only LCoS devices the optical phase modulation of the incident light is a necessary performance parameter and it may be susceptible to small changes in operating temperature, causing significant changes in the output of the corresponding optical diffraction.
Another key challenge in developing next generation LCoS devices is the formation of high-speed multi-level phase modulation. Nematic LCoS devices have demonstrated the benefits of multi-level phase modulation, but are limited by the slow response time of nematic LCs. This is especially true in telecommunications applications where thicker devices are required for the infrared wavelengths used, thus further slowing down the response time. Thus, the main material challenge for these applications is to find suitable high-speed LC materials that can deliver the full 2pi phase depth required in these applications.
There is therefore a need for liquid crystal-based optical components, particularly LCOS devices, that can operate in the visible or infrared region of the electromagnetic spectrum, have improved overall application-related characteristics, have high birefringence and fast switching speeds.
The present invention has been devised in view of the problems of the prior art described herein. Accordingly, it is a general object of the present invention to provide novel and useful materials, devices and techniques that can solve the problems described herein.
One object of the present invention is a liquid-crystalline medium comprising
a) One or more compounds of formula I
Wherein the method comprises the steps of
R 11 R is R 12 Identically or differently represents H, alkyl or alkoxy having 1 to 12C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12C atoms, where one or more CH 2 The radicals can be Instead, and wherein one or more H atoms may be replaced by fluorine,
L 11 、L 12 、L 13 represent H, CH identically or differently 3 Cl or F,
A 11 represents phenylene-1, 4-diyl, wherein, in addition, one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Replacement; cyclohexane-1, 4-diyl or cyclohexene-1, 4-diyl, wherein one or two non-adjacent CH 2 Groups may be replaced independently of one another by O and/or S and one or more H atoms may be replaced by F; bicyclo [1.1.1]Pentane-1, 3-diyl; bicyclo [2.2.2]Octane-1, 4-diyl; spiro [3.3]Heptane-2, 6-diyl; tetrahydropyran-2, 5-diyl; or 1, 3-dioxane-2, 5-diyl,
A 12 representation ofPhenylene-1, 4-diyl, wherein, in addition, one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Alternatively, or in addition, to cyclohexane-1, 4-diyl or cyclohexene-1, 4-diyl, in which one or two are not adjacent CH 2 The radicals may be replaced independently of one another by O and/or S and one or more H atoms may be replaced by F, preferably representing phenylene-1, 4-diyl, wherein one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Alternatively, or in addition, cyclohexane-1, 4-diyl,
Z 1 represents a single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-COO-、-OCO-、-C 2 F 4 -, -cf=cf-, or-ch=chch 2 O-, preferably represents a single bond,
n is 0 or 1, preferably 1;
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b) One or more compounds of the formula T,
wherein the method comprises the steps of
R 1 R is R 2 Represent H, F, cl, br, -CN, -SCN, -NCS, SF 5 Or a linear or branched alkyl group having 1 to 12C atoms, wherein one or more non-adjacent CH 2 The radicals can be such that the O atoms are not directly bonded to one another in each case independently of one another via-CH=CH-, -C.ident.C-, -O-, -CO-O-, -O-CO-O-substitution, and wherein one or more H atoms may be replaced by F, cl or Br,
A T1 、A T2 a is a T3 Each independently of the others represents phenylene-1, 4-diyl, wherein one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Alternatively, wherein
A T1 Alternatively represents cyclohexane-1, 4-diyl, wherein one or two non-adjacent CH 2 Groups may be replaced independently of one another by O and/or S and one or more H atoms may be replaced by F; cyclohexene-1, 4-diyl; bicyclo [1.1.1]Pentane-1, 3-diyl; bicyclo [2.2.2]Octane-1, 4-diyl; spiro [3.3]Heptane-2, 6-diyl; tetrahydropyran-2, 5-diyl; or 1, 3-dioxane-2, 5-diyl,
Z 1 z is as follows 2 Each independently of the other represents-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、-O-CO-、-C 2 H 4 -、-C 2 F 4 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CFHCFH-、-CFHCH 2 -、-CH 2 CFH-、-CF 2 CFH-、-CFHCF 2 -, -CH=CH-, -CF=CH-, -CH=CF-, cf=cf-, -c≡c-, or a single bond, preferably a single bond,
t is 0 or 1, preferably 0;
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c) One or more compounds of formula S1
Wherein the method comprises the steps of
R S1 R is R S2 Represents, identically or differently on each occurrence, H or a straight-chain alkyl radical having from 1 to 25 carbon atoms or a branched alkyl radical having from 3 to 25 carbon atoms, which is unsubstituted or is substituted by CN or CF 3 Monosubstituted or at least monosubstituted by halogen, and wherein one or more CH' s 2 The radicals may each be independently of one another in such a way that the O and/or S atoms are not directly bonded to one another -O-, -S-, -CO-O-, -O-CO-O-, -CH=CH-, or-C≡C-, or halogen, aryl, heteroaryl, alkylaryl or arylalkyl having 6, 5, 7 or 7 to 25 carbon atoms respectively, each of which is unsubstituted or monosubstituted or polysubstituted by alkyl or halogen having 1 to 6C atoms,
s is 0, 1 or 2, and
t is 0, 1, 2 or 3.
According to another aspect of the invention, an electronic component is provided comprising a liquid-crystalline medium according to the invention.
The invention further relates to a device comprising such an electronic assembly.
The invention further relates to the use of a medium as defined above and below in the visible or infrared region of the electromagnetic spectrum, preferably in the region of 420nm to 750nm, or in the a-band and/or B-band and/or C-band, for electro-optical purposes, for phase modulating such visible or infrared light.
The medium according to the invention is characterized by an extremely high birefringence, wherein excellent light stability is observed under blue light irradiation despite the high birefringence. The media are furthermore distinguished in particular by high dielectric anisotropy values and low rotational viscosity. Therefore, the threshold voltage, i.e., the minimum voltage of the switching device, is very low. Low operating voltages and low threshold voltages are needed to enable devices with improved switching characteristics and high energy efficiency. The low rotational viscosity enables fast switching of the assembly and the device according to the invention.
Due to the high clearing temperature, the broad nematic phase range and the excellent Low Temperature Stability (LTS) of the liquid crystal medium used in the optical component according to the invention, the optical component according to the invention is characterized by an excellent operational stability when exposed to the environment. Thus, the assembly and the device containing the assembly can operate under extreme temperature conditions. Surprisingly, the temperature dependence of the birefringence of the liquid-crystalline medium is very small, i.e. the change in Δn with temperature is very small, which makes the device reliable and easy to control.
The medium according to the invention is equally suitable for use in components and devices of high-frequency technology and in applications in the microwave range, in particular for devices for phase shifting microwaves, tunable filters, tunable metamaterial structures and electronic beam-steering antennas, such as phased-array antennas.
Thus, according to another aspect of the invention, there is provided an assembly and a device comprising the assembly, both of which are operable in the microwave region of the electromagnetic spectrum. Preferred components are phase shifters, varactors, wireless and radio wave antenna arrays, matching circuits, and adaptive filters.
Unless explicitly stated otherwise, the following definitions apply.
As used herein, halogen is F, cl, br or I, preferably F or Cl, particularly preferably F.
Herein, alkyl is straight or branched and has 1 to 15C atoms, preferably straight, and has 1, 2, 3, 4, 5, 6 or 7C atoms unless otherwise indicated, and thus is preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.
Branched alkyl is herein alkyl having secondary and/or tertiary, preferably secondary carbon atoms and is preferably isopropyl, sec-butyl, isobutyl, isopentyl, 2-methylhexyl or 2-ethylhexyl, 2-methylpropyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl.
In this context, cyclic alkyl means a cycloaliphatic group or an alkyl group, wherein the methylene group is replaced by a cycloaliphatic group (i.e. cycloalkylalkyl or alkylcycloalkylalkyl), which may be saturated or partially unsaturated, and preferably means cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclopent-1-enyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclopent-1-enylmethyl.
Herein, alkoxy groups are linear or branched and contain 1 to 15C atoms. It is preferably linear and has 1, 2, 3, 4, 5, 6 or 7C atoms unless otherwise indicated, and is therefore preferably methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy or n-heptoxy.
In this context, alkenyl is preferably alkenyl having 2 to 15C atoms, which alkenyl is straight-chain or branched and contains at least one C-C double bond. It is preferably linear and has 2 to 7C atoms. Thus, it is preferably vinyl, prop-1-enyl or prop-2-enyl, but-1-enyl, but-2-enyl or but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl or pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl or hex-5-enyl, hept-1-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl or hept-6-enyl. If two C atoms of the C-C double bond are substituted, the alkenyl group may be in the form of the E and/or Z isomers (trans/cis). In general, the corresponding E isomer is preferred. Among alkenyl groups, prop-2-enyl, but-2-enyl and but-3-enyl and pent-4-enyl are particularly preferred.
Herein, alkynyl means an alkynyl group having 2 to 15C atoms, which is straight or branched and contains at least one c—c triple bond. 1-propynyl and 2-propynyl and 1-butynyl, 2-butynyl and 3-butynyl are preferred.
As used herein, the infrared region of the electromagnetic spectrum means the spectral region of electromagnetic radiation having wavelengths in the range of 0.75 μm to 1000 μm.
As used herein, visible light means light having a wavelength in the range of 420nm to 750 nm.
As used herein, blue light is light having a peak wavelength in the range of 420nm to 490nm, preferably 450nm to 460 nm.
As used herein, infrared a (IR-a) means the spectral region of electromagnetic radiation having a wavelength in the range of 0.75 μm to 1.4 μm.
As used herein, infrared B (IR-B) means the spectral region of electromagnetic radiation having a wavelength in the range of 1.4 μm to 3 μm.
As used herein, infrared C (IR-C) means a spectral region of electromagnetic radiation having a wavelength in the range of 3 μm to 1000 μm.
Preferably, the optical component according to the invention operates at wavelengths in the range 750nm to 2500nm, in particular 1530nm to 1565 nm.
A very preferred light source for the application according to the invention is an IR laser emitting light with a wavelength of 1.55 μm or an IR laser emitting light with a wavelength of 905 nm.
Herein, "high frequency technology" means electromagnetic radiation applications having frequencies in the range of 1MHz to 1THz, preferably 1GHz to 500GHz, more preferably 2GHz to 300GHz, particularly preferably 5GHz to 150 GHz.
The compounds of the formula I are preferably selected from the group of the formulae I-1 to I-3, particularly preferably from the group of the formulae I-3
Wherein the radicals present have the corresponding meanings given in accordance with formula I above, and in formulae I-1 and I-2, preference is given to:
R 11 n-alkyl or alkenyl having up to 7C atoms, most preferably n-alkyl having 1 to 5C atoms, and
R 12 n-alkoxy or alkenyloxy having 1 to 6C atoms, most preferably n-alkoxy having 1 to 4C atoms, and
in formula I-3, preference is given to
R 11 N-alkyl or alkenyl having up to 7C atoms, most preferably n-alkyl having 1 to 5C atoms, and
R 12 an n-alkyl or alkenyl group having up to 7C atoms, most preferably an n-alkyl group having up to 5C atoms.
The liquid-crystalline medium according to the invention preferably comprises one or more compounds of the formula I-1, preferably selected from the group of compounds of the formulae I-1a to I-1d, preferably of the formulae I-1a and/or I-1d, most preferably of the formulae I-1a,
wherein R is 11 R is R 12 Having the meaning given above.
The liquid-crystalline medium according to the invention preferably comprises one or more compounds of the formula I-2, preferably selected from the group of compounds of the formulae I-2a to I-2f, preferably of the formulae I-2a and/or I-2d, most preferably of the formulae I-2a,
Wherein R is 11 R is R 12 Having the meaning given above.
The liquid-crystalline medium according to the invention preferably comprises one or more compounds of the formula I-3, preferably selected from the group of compounds of the formulae I-3a to I-3d, preferably of the formulae I-3a and/or I-3c and/or I-3d, most preferably of the formulae I-3d,
wherein R is 11 R is R 12 Having the meaning given above.
Preferably the compound of formula T is selected from the group of formulae T1 to T5, very preferably the compound of formula T1:
wherein R is 1 R is R 2 Has the meaning indicated above for formula T, and L 2 、L 3 、L 4 、L 5 L and L 6 And represents H or F. Preferably L 2 Represents F and L 4 、L 5 L and L 6 Represents H and L 3 And represents H or F.
Very preferably, the compounds of formula S1 are those as follows: wherein R is S2 At least one of the radicals is a linear or branched alkyl radical having from 1 to 15 carbon atoms, where in addition one or more CH 2 The radical may be replaced by-COO-or-O-CO-and is an aryl or alkylaryl group having from 5 to 15 carbon atoms, and X is preferably H or Cl. Very particular preference is given to R S2 The radicals are methyl, tert-butyl, 2-butyl, 1-dimethylpropyl, 1, 2-tetramethylpropyl and 1-methyl-1-phenylethyl.
The compound of formula S1 is preferably selected from compounds of formula S1-1:
wherein the method comprises the steps of
R S1 H, F or Cl, preferably H or Cl, and
R 21 r is R 22 Same or different represents H or a straight-chain or branched alkyl radical having 1 to 12 carbon atoms, in which one or more CH 2 The radicals may be each independently of the other so that the O atoms are not directly bonded to one another-O-, -CO-O-, -O-CO-, -ch=ch-, or-c≡c-, or aryl or aralkyl having 6 to 25 carbon atoms.
Particularly preferred are compounds of formula S1-1 selected from the following formulae:
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or a mixture of these compounds. Particularly preferred are compounds of the formula S1-1 a.
Other suitable UV stabilizers are selected from the following formulas:
in a preferred embodiment of the invention, the medium comprises one or more compounds selected from the group consisting of the formulae S2 and S3:
wherein the method comprises the steps of
q is 1, 2, 3 or 4, preferably 2, 3 or 4, very preferably 2 or 4,
g represents a hydrocarbon group having 1 to 60 carbon atoms, which may be straight-chain or branched or cyclic, and which is unsubstituted or substituted by CN or CF 3 Monosubstituted or at least monosubstituted by halogen, and wherein one or more CH' s 2 The radicals may be such that O or S atoms are not directly bonded to one another and are each independently of one another via-O-, -S-, -NR 0 -, -CO-O-; -O-CO- -O-CO-O-, -CH=CH-or-C≡C-substitution,
R 0 represents an alkyl group having 1 to 6C atoms,
R 2 represents H, -O, -OH, a linear or branched or cyclic alkyl or alkoxy or arylalkoxy group each having 1 to 12C atoms, preferably H or-O,
R 21 R is R 22 Identically or differently represents a linear or branched alkyl residue having 1 to 12 carbon atoms, or R 21 R is R 22 Together with the carbon atoms to which it is attached form cycloalkyl groups having 5 to 12 carbon atoms,
R 23 r is R 24 Identically or differently represents a linear or branched alkyl residue having 1 to 12 carbon atoms, or R 23 R is R 24 Together with the carbon atoms to which it is attached form cycloalkyl groups having 5 to 12 carbon atoms,
Z 2 represents, identically or differently, at each occurrence, -O- >,c (O) O-, OC (O) -or a single bond,
R ST represents H, alkyl or alkoxy having 1 to 12C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12C atoms, where one or more CH 2 The radicals can beInstead, and wherein one or more H atoms may be replaced by fluorine,
Z ST each independently of the other represents-CO-O-; -O-CO-, -CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CH 2 -、-CH 2 CH 2 、-(CH 2 ) 4 -、-CH＝CH-CH 2 O-、-C 2 F 4 -、-CH 2 CF 2 -、-CF 2 CH 2 -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C.ident.C-or a single bond,
which on each occurrence, are identical or different and represent cyclohexane-1, 4-diyl, cyclohexene-1, 4-diyl, pyran-2, 5-diyl or 1, 3-dioxane-2-5-diyl, wherein one or more H atoms may be replaced by F,
p is 0, 1 or 2.
In formula S2, when q is 2, G may be a divalent straight or branched aliphatic residue (saturated or unsaturated) having 2 to 20 carbon atoms, a divalent alicyclic residue having 5 to 20 carbon atoms, a divalent aralkyl residue having 8 to 20 carbon atoms, or a divalent aryl residue having 6 to 20 carbon atoms.
When q is 2, examples of the group G are 1, 2-ethylene, 1, 2-propylene, 1, 4-n-butylene, 1, 3-butylene, 1, 6-n-hexylene, 1, 7-n-heptylene, 1, 10-n-decylene, 1, 12-n-dodecylene, 2-dimethyl-1, 3-propylene, 1,2, 3-trimethyl-1, 4-butylene, 3-thia-1, 5-pentylene, 3-oxa-1, 5-pentylene, 1, 4-but-2-ene, 1, 4-but-2-yne, 2, 5-hex-3-ene, 1, 2-cyclohexylene, 1, 3-cyclohexylene, 1, 4-cyclohexylene, hexahydro-p-xylene, m-xylene, 1, 2-phenylene, 1, 4-phenylene, 2 '-biphenylene, 4' -biphenylene, 2, 6-naphtylene and 2, 7-fluoroethylene (fluoroethylene).
In formula S2, when q is 3, G may be a trivalent straight or branched aliphatic (saturated or unsaturated) residue having 3 to 15 carbon atoms, a trivalent alicyclic residue having 5 to 15 carbon atoms, a trivalent aralkyl residue having 9 to 15 carbon atoms, or a trivalent aryl residue having 6 to 16 carbon atoms.
When q is 3, examples of the group G are 1,2, 3-trisubstituted propane, 1,2, 4-trisubstituted butane, 2, 5-dimethyl-1, 2, 6-trisubstituted hexane, 1-trimethylene-propane, 1,2, 3-trisubstituted cyclohexane, 1,3, 5-trimethylene benzene and 1,2, 7-trisubstituted anthracene.
In formula S2, when q is 4, G may be a linear or branched tetravalent aliphatic residue (saturated or unsaturated) having 4 to 60 carbon atoms or a tetravalent alicyclic residue having 5 to 60 carbon atoms, such as tetramethylene methane or 1, 4-tetramethylene cyclohexane, or arylene-tetraalkylene or arylalkylaryl-tetraalkylene.
When n is 2, 3 or 4 and G is an aliphatic or alicyclic residue, each of these residues may be unsubstituted or substituted with halogen or interrupted by one or more oxygen or sulfur atoms or aryl or aralkyl residues. Aryl groups include fused rings such as naphthalene and one, two, three or more aryl groups linked via a single bond or alkylene.
Group R 21 R is R 22 R is as follows 23 R is R 24 Examples of (2) are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, n-hexyl, n-dodecyl or together with R 21 R is R 22 R is as follows 23 R is R 24 The bonded carbon may form, for exampleIs a group of (2).
Particularly preferred substituents R 21 R is R 22 R is as follows 23 R is R 24 Is a straight or branched alkyl group having 1 to 4 carbon atoms, most preferablyIs methyl.
Very preferably, the compound of formula S2 is selected from the group consisting of the subformulae S2-1 and S2-2
Wherein G represents a divalent aliphatic or cycloaliphatic group having 1 to 20C atoms.
Examples of the group G in the formula S2-1 or S2-2 are optionally methylene, ethylene or polymethylene having up to 20 carbon atoms; or one or two hetero atoms between alkylene groups, e.g. divalent radicals-CH 2 OCH 2 -、-CH 2 CH 2 OCH 2 CH 2 -、-CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 -、-CH 2 C(O)OCH 2 CH 2 O(O)CCH 2 -、-CH 2 CH 2 C(O)OCH 2 CH 2 O(O)CCH 2 CH 2 -、-CH 2 CH 2 -C(O)O(CH 2 ) 4 O(O)C-CH 2 CH 2 -、-CH 2 CH 2 O(O)C(CH 2 ) 4 C(O)OCH 2 CH 2 -and-CH 2 CH 2 O(O)C(CH 2 ) 8 C(O)OCH 2 CH 2 -。
G may also be an arylene-dialkylene group such as p-xylene, benzene-1, 3-bis (ethylene), biphenyl-4, 4' -bis (methylene) or naphthalene-1, 4-bis (methylene).
Other very preferably the compound of formula S2 is selected from the group consisting of compounds of formula S2-3
Wherein the method comprises the steps of
Sp, which in each occurrence are identical or different, represents a linear or branched alkylene radical having 1 to 12C atoms, where one or more CH 2 The groups may be replaced by O in such a way that O atoms are not directly bonded to each other, or represent single bonds.
Particularly preferably, the medium comprises one or more compounds of the formula S2-1a or S2-2a, preferably S2-1a
Wherein the method comprises the steps of
R S3 Represents H or an alkyl group having 1 to 6C atoms, preferably H or ethyl;
t is 0 or 1, and
q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
r is 2, 3, 4, 5, 6, 7 or 8, and
s is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.
Particularly preferably, the compounds of the formula S2 are selected from the group consisting of compounds of the formulae S2-1a-1, S2-1a-2, S2-2a-1 and S2-3 a-1. These compounds are characterized by very good solubility in the liquid-crystalline medium.
Other preferred examples of compounds of formula S2 are the following:
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wherein R is 2 Has the meaning given above and preferably represents H or-O-.
Of the compounds of the formula S3, particular preference is given to compounds of the formulae S3-1 to S3-4
Wherein n=1, 2, 3, 4, 5, 6 or 7, preferably n=1 or 7
Wherein n=1, 2, 3, 4, 5, 6 or 7, preferably n=3
Wherein n=1, 2, 3, 4, 5, 6 or 7, preferably n=3
In a preferred embodiment, the medium according to the invention comprises one or more compounds selected from the group consisting of formulae II and III:
wherein the method comprises the steps of
R 2 R is R 3 Represents unsubstituted or halogenated, straight-chain or branched alkyl or alkoxy having 1 to 15C atoms, wherein one or more CH of these groups 2 The radicals may be each independently of the other so that the O atoms are not directly bonded to one another -C≡C-、-CF 2 O-, -CH=CH-, -O-, -CO-O-, or-O-CO-, substitution,
to->Is->To->The same or different expressions
Preferred representation
L 21 、L 22 、L 31 L and L 32 Identically or differently, H or F, preferably F,
Y 2 y and Y 3 Identically or differently represent H or CH 3 ，
X 2 X is X 3 Identically or differently halogen, halogenated alkyl or alkoxy having 1 to 3C atoms or halogenated alkenyl or alkenyloxy having 2 or 3C atoms, preferably F, cl, OCF 3 Or CF (CF) 3 Most preferably, the representation F, CF 3 Or OCF (optical clear) 3 ，
Z 3 represents-CH 2 CH 2 -、-CF 2 CF 2 -, -COO-, trans-ch=ch-, trans-cf=cf-, -CH 2 O-or a single bond, preferably represents-CH 2 CH 2 -, -COO-, trans-CH=CH-or a single bond, and most preferably represents-COO-, trans-ch=ch-, or a single bond, and
l, m, n and o are each independently of the other 0 or 1,
preferably, l+m is 2.
Preferably, the medium comprises one or more compounds of the formula II, preferably selected from the group of compounds of the formulae II-1 to II-3, very preferably selected from the group of compounds of the formulae II-1 and II-3
Wherein the radicals present have the corresponding meanings as given in formula II and in formula II-1 above, a radical L 23 L and L 24 Independently of each other and independently of the other parameters, H or F, and in the formula II-2, preferably
Is->Are independently of each other represent
In the formulae II-1, II-2 and II-3, L 21 L and L 22 Or L 23 L and L 24 Preferably F.
In another preferred embodiment in formulae II-1 and II-2, L 21 、L 22 、L 23 L and L 24 All represent F.
The compounds of the formula II-1 are preferably selected from the group of compounds of the formulae II-1a to II-1h, preferably II-1a, II-1b, II-1g and II-1h
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Wherein the radicals present have the corresponding meanings given above.
In a preferred embodiment of the invention, the medium comprises one or more compounds selected from the group of compounds of the formulae II-1a to II-1h, wherein L 21 L and L 22 And/or L 23 L and L 24 F is respectively adopted.
In another preferred embodiment, the medium comprises a compound selected from the group of compounds of formulae II-1a to II-1h, wherein L 21 、L 22 、L 23 L and L 24 All are F.
Particularly preferred compounds of the formula II-1 are
Wherein R is 2 Having the meaning given above.
Preferably, the compound of formula II-2 is selected from the group of compounds of formulas II-2a to II-2c
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Wherein the radicals present have the corresponding meanings given above, and preferably L 21 L and L 22 All are F.
Preferably, the compounds of formula II-3 are selected from the group of compounds of formulae II-3a to II-3e, preferably II-3d and II-3e
Wherein the radicals present have the corresponding meanings given above, and preferably L 21 L and L 22 Are all F and L 23 L and L 24 Are all H, or L 21 、L 22 、L 23 L and L 24 All are F.
Particularly preferred compounds of the formula II-3 are
Wherein R is 2 Having the meaning given above.
Very particular preference is given to compounds of the formula II-3 d-1.
In addition to the preferred compounds of formula II above, the medium optionally comprises one or more compounds of formula II selected from compounds of formulae IIA1 to IIA 7:
wherein R is 2 X is X 2 Having the meaning given in formula II or one of the preferred meanings given above and below.
Preferred compounds are those of formulae IIA1, IIA2 and IIA3, very preferably those of formulae IIA1 and IIA 2.
In the compounds of formulae IIA1 to IIA7, R 2 Preferably represents alkyl having 1 to 6C atoms, very preferably represents ethyl or propyl, and X 2 Preferably F or OCF 3 Very preferably represents F.
In another preferred embodiment of the invention, the medium comprises one or more compounds of formula III, preferably selected from the group of compounds of formulae III-1 and III-2, preferably III-2:
wherein the radicals and parameters present have the corresponding meanings given in accordance with formula III above.
Preferably, the compound of formula III-1 is selected from the group of compounds of formulae III-1a and III-1b
Wherein the radicals present have the corresponding meanings given above and L 33 L and L 34 Independently of each other, H or F.
The compound of formula III-1a is preferably selected from the group of compounds of formulae III-1a-1 to III-1a-6
Wherein R is 3 Having the meaning given above.
Preferably, the compound of formula III-2 is selected from the group of compounds of formulae III-2a to III-2m
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Wherein the radicals present have the corresponding meanings given above and L 35 L and L 36 Independently of each other, H or F.
Preferably, the compound of formula II-2a is selected from the group of compounds of formulae III-2a-1 to III-2a-4
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Wherein R is 3 Having the meaning given above.
The compound of formula III-2b is preferably selected from the group of compounds of formulae III-2b-1 and III-2b-2, preferably III-2b-2
Wherein R is 3 Having the meaning given above.
The compounds of the formula II-2c are preferably selected from the group of compounds of the formulae III-2c-1 to III-2c-5
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Wherein R is 3 Having the meaning given above.
The compounds of the formulae III-2d and III-2e are preferably selected from the group of compounds of the formulae III-2d-1, III-2d-2 and III-2e-1
Wherein R is 3 Having the meaning given above.
The compound of formula III-2f is preferably selected from the group of compounds of formulae III-2f-1 to III-2f-7
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The compound of formula III-2g is preferably selected from the group of compounds of formulae III-2g-1 to III-2g-7
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Wherein R is 3 Having the meaning given above.
The compound of formula III-2h is preferably selected from the group of compounds of formulae III-2h-1 to III-2h-5
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Wherein R is 3 Having the meaning given above.
The compound of formula III-2i is preferably selected from the group of compounds of formulae III-2i-1 to III-2i-3
Wherein R is 3 Having the meaning given above.
The compound of formula III-2j is preferably selected from the group of compounds of formulae III-2j-1 to III-2j-3
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Wherein R is 3 Having the meaning given above.
The compound of formula III-2k is preferably selected from the group of compounds of formulae III-2k-1 to III-2k-6
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Wherein R is 3 Having the meaning given above.
The compound of formula III-2l is preferably selected from the group of compounds of formulae III-2l-1 to III-2l-6
Wherein R is 3 Having the meaning given above.
The compound of formula III-2m is preferably selected from compounds of formula III-2 m-1:
Alternatively or in addition to the compounds of the formulae III-1 and/or III-2, the medium according to the invention optionally comprises one or more compounds of the formula III-3,
wherein the radicals and parameters have the corresponding meanings given in accordance with formula III above, preferably compounds of formula III-3a
Wherein R is 3 Having the meaning given above.
In addition to the preferred compounds of formula III above, the medium optionally comprises one or more compounds selected from the group consisting of formulas IIIA-1 to IIIA-21:
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wherein R is 3 X is X 3 Having the meaning given in formula III or one of the preferred meanings given above and below. Preferred compounds are those of the formulae IIIA1, IIIA4, IIIA6, IIIA16, IIIA19 and IIIA 20.
Preferably, the medium according to the invention comprises one or more compounds of formula IV
Wherein the method comprises the steps of
R 41 Represents a linear alkyl group having 1 to 12C atoms or a branched or cyclic alkyl group having 3 to 12C atoms, or a linear alkenyl group having 2 to 12C atoms or a branched alkenyl group having 3 to 12C atomsA group or a cyclic alkenyl group having 5 to 12C atoms, wherein one or more H atoms are optionally replaced by fluorine, preferably represents a straight-chain alkenyl group having 2 to 12C atoms,
R 42 represents a linear alkyl or alkoxy group having 1 to 12C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 12C atoms, or a linear alkenyl group having 2 to 12C atoms or a branched alkenyl group having 3 to 12C atoms or a cyclic alkenyl group having 5 to 12C atoms, wherein one or more H atoms are optionally replaced by fluorine, preferably represents a linear alkyl group having 1 to 12C atoms, very preferably having 1 to 7C atoms.
The compound of formula IV is preferably selected from the group of compounds of formulae IV-1 to IV-4, very preferably IV-3:
wherein the method comprises the steps of
The alkyl and alkyl' independently of one another represent alkyl groups having 1 to 7C atoms, preferably having 2 to 5C atoms,
alkoxy denotes an alkoxy group having 1 to 5C atoms, preferably having 2 to 4C atoms,
alkinyl represents an alkenyl radical having 2 to 5C atoms, preferably having 2 to 4C atoms, particularly preferably having 2C atoms, and
alkinyl' represents an alkenyl radical having 2 to 5C atoms, preferably having 2 to 4C atoms, particularly preferably having 2 to 3C atoms.
In a preferred embodiment, the medium according to the invention comprises a combination of one or more compounds of formula IV selected from the group of compounds of formulae IV-1 to IV-4 and one or more compounds selected from the group of compounds of formulae IVA-1 to IVA-18:
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wherein alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or n-pentyl.
Preferably, the medium comprises one or more compounds of formula IV-1, preferably selected from the group consisting of compounds of formulae IV-1-1 to IV-1-6
Preferably, the medium according to the invention comprises one or more compounds of the formulae IV-2-1 and/or IV-2-2
Preferably, the medium according to the invention comprises a compound of formula IV-3, very preferably selected from compounds of formulae IV-3-1 to IV-3-6, in particular compounds of formulae IV-3-2 and/or IV-3-6:
Preferably, the medium according to the invention comprises a compound of formula IV-4, in particular a compound selected from the group consisting of formula IV-4-1 and IV-4-2:
preferably, the medium according to the invention comprises one or more compounds of the formulae IVa and/or IVb
Wherein the method comprises the steps of
R 41 R is R 42 Independently of one another, have the meanings defined above for the formula IV, andrepresentation of
Z 4 Represents a single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-COO-、-OCO-、-C 2 F 4 -、-C 4 H 8 -or-cf=cf-.
Preferably, the compound of formula IVa is selected from compounds of formulae IVa-1 to IVa-4:
wherein the method comprises the steps of
The alkyl and alkyl each independently represent a straight chain alkyl group having 1 to 6C atoms.
The medium according to the invention preferably comprises at least one compound of formula IVa-2.
Preferably the compound of formula IVb is selected from compounds of formulae IVb-1 to IVb-3:
wherein the method comprises the steps of
alkyl and alkyl each independently of the other represent a linear alkyl radical having 1 to 6C atoms, and
each of alkinyl represents, independently of the others, a straight-chain alkenyl group having 2 to 6C atoms.
Of the compounds of the formulae IVb-1 to IVb-3, compounds of the formula IVb-2 are particularly preferred.
Particularly preferred compounds of formula IVb are selected from the following compounds:
the medium according to the invention particularly preferably comprises compound IVb-2-3.
Preferably, the medium according to the invention comprises one or more compounds of formula V
Wherein the method comprises the steps of
R 51 、R 52 Represents alkyl having 1 to 7C atoms, alkoxy having 1 to 7C atoms or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7C atoms,
The same or different expressions
Z 51 、Z 52 Each independently of the other represents-CH 2 -CH 2 -、-CH 2 -O-, -CH=CH-, -C≡C-, -COO-, or a single bond, and
n is 1 or 2.
The compounds of formula V are preferably selected from compounds of formulae V-1 to V-17:
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wherein R is 1 R is R 2 Having the meaning indicated above for formula V.
R 1 R is R 2 Preferably each independently of the other represents a straight-chain alkyl group having 1 to 7C atoms or an alkenyl group having 2 to 7C atoms.
Preferred media comprise one or more compounds of the formulae V-10, V-11, V-12, V-14, V-15, V-16 and/or V-17. Very preferably, the medium comprises one or more compounds of the formulae V-10, V-16 and/or V-17, in particular V-10 and V-17.
In a preferred embodiment of the invention, the medium additionally comprises one or more compounds of the formulae VI-1 to VI-9
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Wherein the method comprises the steps of
R 7 Each, independently of the other, has the meaning as set forth in claim 5 for R 2A One of the indicated meanings, and w and x each independently of one another denote 1 to 6.
Particularly preferred are mixtures comprising at least one compound of the formula V-9.
In a preferred embodiment of the invention, the medium additionally comprises one or more compounds of the formulae VII-1 to VII-21
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Wherein the method comprises the steps of
R represents a linear alkyl or alkoxy radical having 1 to 6C atoms, (O) represents-O-or a single bond, and m is 0, 1, 2, 3, 4, 5 or 6, and n is 0, 1, 2, 3 or 4, and R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.
Particularly preferred are compounds of the formulae VII-1, VII-2, VII-4, VII-20 and VII-21. In these compounds, R preferably represents an alkyl group each having 1 to 5C atoms, and further represents an alkoxy group. In the compounds of the formulae VII-20, R preferably represents alkyl or alkenyl, in particular alkyl. In the compounds of the formula VII-21, R preferably represents alkyl.
In one embodiment of the invention, the clearing point of the liquid crystal medium is preferably 70 ℃ or more, more preferably 75 ℃ or more, still more preferably 80 ℃ or more or 85 ℃ or more, very preferably 90 ℃ or more, particularly preferably 100 ℃ or more.
In one embodiment, the medium comprises
One or more compounds of the formula I in a total concentration in the range from 10% to 60%, preferably from 15% to 55%, more preferably from 30% to 40%,
a kind of electronic device with high-pressure air-conditioning system
One or more compounds of formula T in a total concentration in the range from 5% to 25%, preferably from 8% to 15%, more preferably from 10% to 20%,
a kind of electronic device with high-pressure air-conditioning system
-one or more compounds of formula S1 in a total concentration of more than 0% to 3%, preferably 0.1% to 2%, more preferably 0.15% to 1.5% and in particular 0.2% to 1%;
a kind of electronic device with high-pressure air-conditioning system
Preferably one or more compounds of formula II and/or III, more preferably formula II, wherein the total concentration of compounds of formula II and/or III is in the range of 15% to 45%, preferably 20% to 40%, more preferably 25% to 35%; the compounds of formula II are preferably selected from the group consisting of formulae II-1a and II-1g and II-3d; very preferably, the medium comprises one or more compounds of the formulae II-1a and/or II-1g in a total concentration of from 10% to 20%, in particular from 12% to 17%, and one or more compounds of the formula II-3d in a total concentration of from 10% to 20%, in particular from 12% to 17%;
And/or
Preferably one or more compounds of formula IV, more preferably formula IV-3, wherein the total concentration of compounds of formula IV is in the range of 5 to 25%, preferably 7 to 20%, very preferably 12 to 17%; or one or more compounds of the formulae IV and IVa, preferably IV-3 and IVa-2, wherein the total concentration of the compounds of the formula IV is in the range from 2 to 20%, preferably 5 to 15%, very preferably 8 to 12% and the total concentration of the compounds of the formula IVa is in the range from 5 to 25%, preferably 7 to 20%, very preferably 12 to 17%, and wherein the total concentration of the compounds of the formula IV and IVa is preferably in the range from 10 to 40%, more preferably 15 to 35%, very preferably 20 to 30%.
In a preferred embodiment, the liquid-crystalline medium according to the invention has a positive dielectric anisotropy Δεranging from 6.0 to 20.0, preferably from 8.0 to 17.0, and in particular from 10 to 13.
In a preferred embodiment, the metal oxide is doped at 589nm (Na D ) And a birefringence (Δn) of the liquid-crystalline medium according to the invention in the range from 0.180 to 0.400, preferably from 0.190 to 0.310, more preferably from 0.200 to 0.300, very preferably from 0.210 to 0.260, at 20 ℃.
In another embodiment, the medium comprises
One or more compounds of formula I in a concentration in the range of 15% to 65%, preferably 20% to 60%, and more preferably 35% to 45%,
A kind of electronic device with high-pressure air-conditioning system
-one or more compounds of formula T in a total concentration ranging from 2% to 30%, preferably from 5% to 25%, more preferably from 7% to 18%, very preferably from 8% to 13%, and
-one or more compounds of formula S1 in a total concentration higher than 0% to 3%, preferably 0.1% to 2%, more preferably 0.15% to 1.5% and in particular 0.2% to 1%, and
preferably one or more compounds of formula II and/or III, more preferably formula II, wherein the total concentration of compounds of formula II and/or III is in the range of 5% to 30%, preferably 8% to 20%, more preferably 10% to 16%; the compounds of formula II are preferably selected from the group consisting of formulae II-1a and II-1g and II-3d; very preferably, the medium comprises one or more compounds of the formulae II-1a and/or II-1g in a total concentration of from 2% to 15%, in particular from 8% to 10%, and one or more compounds of the formula II-3d in a total concentration of from 1% to 10%, in particular from 2% to 7%;
and/or
Preferably one or more compounds of formula IV, preferably formula IV-3, wherein the total concentration of the compounds of formula IV is in the range of 3 to 20%, preferably 5 to 15%, very preferably 7 to 12%;
and/or
Preferably, the total concentration of the one or more compounds of formula V is in the range of 5% to 30%, more preferably 8% to 25%, very preferably 12% to 18%, preferably selected from the group consisting of compounds of formulae V-10 and V-17, wherein the total concentration of the compounds of formula V-10 is in the range of 2% to 20%, more preferably 4% to 13%, very preferably 5% to 10%, and wherein the total concentration of the compounds of formula V-17 is in the range of 2% to 20%, more preferably 4% to 13%, very preferably 5% to 10%.
In a preferred embodiment, the liquid-crystalline medium according to the invention has a positive dielectric anisotropy Δεranging from 2.0 to 6.0, preferably from 3.0 to 5.0, and in particular from 3.5 to 4.5.
In a preferred embodiment of the invention, the liquid-crystalline medium has a clearing point of 120℃or more, preferably 130℃or more, particularly preferably 140℃or more and very particularly preferably 150℃or more.
The nematic phase of the medium according to the invention preferably extends at least from 0 ℃ or lower to 90 ℃ or higher. It is advantageous for the medium according to the invention to exhibit an even broader nematic phase range, which is preferably at least-10 ℃ or lower to 120 ℃ or lower, very preferably at least-20 ℃ or lower to 140 ℃ or higher and in particular at least-30 ℃ or lower to 150 ℃ or higher, very particularly preferably at least-40 ℃ or lower to 170 ℃ or higher.
The medium according to the invention has a tunability τ of 0.200 or more, preferably 0.210 or more, measured at 20 ℃ and 19 GHz.
Preferably the liquid crystal material has a material quality (η) of 6 or more, preferably 8 or more, very preferably 10 or more, in particular 15 or more.
In the corresponding component, it is preferable that the phase shifter quality of the liquid crystal material is 15 °/dB or more, preferably 20 °/dB or more, preferably 30 °/dB or more, preferably 40 °/dB or more, preferably 50 °/dB or more, particularly preferably 80 °/dB or more and very particularly preferably 100 °/dB or more.
An electronic component is provided comprising a first substrate and a second substrate facing each other, wherein a liquid crystal medium according to the invention is sandwiched between the first substrate and the second substrate, and an electrode provided on each substrate or two electrodes provided on only one of the substrates for providing an electric potential across the liquid crystal material for driving a liquid crystal of a predetermined configuration.
In one embodiment, the electronic component is operable in the microwave range of the electromagnetic spectrum. Here, the liquid crystal medium in the assembly acts as a tunable dielectric and can be used in high frequency technology.
Preferred components are liquid crystal based antenna components, phase shifters, tunable filters, tunable metamaterial structures, matching networks or varactors.
A microwave antenna array is provided that includes one or more of the components.
In another embodiment, the electronic component is an optical component operable in the visible or infrared range of the electromagnetic spectrum, preferably a transmissive SLM.
In another preferred embodiment, the optical component is a reflective SLM.
In an optical device assembly according to the invention, the light modulating assembly (i.e. the pixel) of the spatial light modulator is a cell containing a liquid crystal as claimed in claim 1. That is, the spatial light modulator is a liquid crystal device in which the optically active component is a liquid crystal. Each liquid crystal cell is configured to selectively provide a plurality of light modulation levels (light modulation level). That is, each liquid crystal cell is configured at any one time to operate at one light modulation level selected from a plurality of possible light modulation levels. Each liquid crystal cell is dynamically reconfigurable to a different light modulation level than the plurality of light modulation levels.
LCOS devices provide a dense array of light modulating components or pixels within a small aperture (e.g., a few centimeters in width). The pixels are typically about 10 microns or less, which creates a diffraction angle of a few degrees, which means that the optical system can be compact. LCOS devices are typically reflective, meaning that the circuitry driving the pixels of the LCOS SLM can be buried under a reflective surface. This results in a higher void ratio. In other words, the pixels are closely packed, which means that there is little dead space between the pixels. This is advantageous because it reduces optical noise in the playback field. LCOS SLMs use a silicon back plate, which has the advantage that the pixels are optically flat. This is particularly important for phase modulation devices.
Accordingly, in a preferred embodiment and referring to FIG. 1, there is provided a reflective spatial light modulator, in particular an LCoS device 100, comprising a liquid crystal material 140 as defined above sandwiched between a transparent glass layer 110 having transparent electrodes 120 and a mirror 150 mounted on a silicon CMOS backplate 160 and PCB mount (not shown). The mirror is divided into a two-dimensional array of individually addressable pixels. Each pixel is individually drivable by a voltage signal to provide a local phase change to at least one polarization component of the optical signal, thereby providing a two-dimensional array of phase-manipulating regions. The pre-alignment of the liquid crystal 140 is provided by the alignment layers 131 and 132.
The LCOS device is suitable for integration into an optical device. The described LCOS SLM outputs spatially modulated light in a reflective manner. Reflective LCOS SLMs have the advantage that the signal lines, gate lines, and transistors are below the mirrored surface, which results in high fill factor (typically greater than 90%) and high resolution. Another advantage of using a reflective LCOS spatial light modulator is that the liquid crystal layer can be half of the thickness than is required when using a transmissive device. This greatly improves the switching speed of the liquid crystal (a key advantage of projection of moving video images). However, the teachings of the present invention may equally be implemented using transmissive LCOS SLMs.
An example of a device comprising an optical component according to the invention is a holographic projector; a heads-up display comprising at least one holographic projection channel; the driver monitoring system of the head up display, more preferably an infrared holographic projector for the driver monitoring system of the head up display; an augmented reality head-up display "AR-HUD" including eye-movement tracking or head-tracking; an image generation unit; and an integrated infrared holographic illuminator for head tracking or eye movement tracking.
The spatial light modulator may be used to display a diffraction pattern comprising a computer-generated hologram. If the hologram is a phase-only hologram, a spatial light modulator that modulates the phase is required. If the hologram is a full-complex hologram, a spatial light modulator that modulates phase and amplitude may be used or a first spatial light modulator that modulates phase and a second spatial light modulator that modulates amplitude may be used.
Other preferred devices are infrared imagers, wavelength selective switches, LCoS-SLMs, LIDAR systems, wavelength Division Multiplexing (WDM) systems, reconfigurable Optical Add Drop Multiplexers (ROADMs) and non-mechanical beam steering, such as steerable electric transient optical refractive (SEEOR) prisms, as disclosed in chapter p.mcmanamon,2006, "Agile Nonmechanical Beam Steering," opt.photon.news 17 (3): 24-29.
This technique combines an SLM device with a red-green-blue (RGB) light source. Red-green-blue (RGB) light sources are configured to emit red, green, and blue light (e.g., time multiplexed RGB LEDs or laser diodes) at the same time or at different times. As one example, the light source is an RGB light source using an array of red, green and blue micro LEDs, as proposed in e.g. EP3539157 A1.
RGB refers to the three primary colors of light, red, green and blue, whereby other colors and white can be formed. A conventional single LED may only transmit monochromatic (single-color) light, which may be one of these three primary colors. To create more colors, three LEDs may be used together for RGB mixing. RGB LEDs are in principle three monochromatic LEDs placed close to each other, usually in the same package, and with the colors red, green and blue. When all the LEDs of the RGB-LED emit light with the same luminous intensity in proportion and the correct kind of optical component is used, the light emitted by the RGB-LED appears white to the human eye.
The use of an RGB light source avoids exposure of the liquid crystal to UV light, which is unavoidable when using conventional light sources, such as cold cathode fluorescent lamps.
Thus, according to another aspect of the present invention, there is provided an optical device comprising an RGB light source and an optical assembly as described above, wherein the phase of an incident optical signal from the RGB light source is modulated by the assembly when the optical device is in operation.
According to another aspect of the present invention, there is provided a method of spatially modulating visible or infrared light, the method comprising,
i) Providing an optical assembly comprising first and second substrates facing each other and each having a surface, the first substrate comprising at least one first electrode, the second substrate comprising at least one second electrode, the assembly further comprising a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises one or more compounds selected from the group consisting of compounds of formulae I, T and S1 above;
ii) receiving incident visible or infrared light at a surface of the optical component;
iii) A predetermined voltage is applied to each of the individual electrodes formed on the first substrate so as to modulate the refractive index of the liquid crystal layer.
According to another aspect of the present invention, there is provided a method of manufacturing an optical phase modulator comprising at least the steps of
a) Providing a first substrate having a first electrode, optionally having a two-dimensional array of individually electrically drivable cartridges (electrically drivable cell);
b) Depositing the liquid-crystalline medium of claim 1 on a first substrate; a kind of electronic device with high-pressure air-conditioning system
c) A second substrate having a second electrode is mounted to the liquid crystal material.
The liquid-crystalline medium according to the invention consists of a plurality of compounds, preferably 3 to 30, more preferably 4 to 20 and very preferably 4 to 16 compounds. These compounds are mixed in a conventional manner. In general, the desired amount of the compound used in a smaller amount is dissolved in the compound used in a larger amount. Completion of the dissolution process is particularly readily observed if the temperature is above the clearing point of the compound used at higher concentrations. However, it is also possible to prepare the medium in other conventional ways, for example using so-called premixes, which may be, for example, homologous or eutectic mixtures of compounds, or using so-called "multi-bottle" systems, the components of which are themselves ready-to-use mixtures.
In the present invention and in particular in the examples below, the structure of the mesogenic compounds is indicated by abbreviations or acronyms. In these acronyms, the following tables a to C are used, and the chemical abbreviations are as follows. All radicals C n H 2n+1 、C m H 2m+1 C (C) l H 2l+1 C n H 2n-1 、C m H 2m-1 C (C) l H 2l-1 Respectively represent a linear alkyl or alkylene group, in each case having n, m or l C atoms, where n and m are independently 1, 2, 3, 4, 5, 6 or 7 and l is 1, 2 or 3. Table A lists the codes for the ring elements of the core structure of the compounds, while Table B shows the linking groups and end groups. Table C shows the illustrative structures of the compounds and their corresponding abbreviations.
Table a: ring element
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Table B: bonding group
Table B: end group
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Used in combination with other
Where n and m each represent integers, and three-point "." is a placeholder for other abbreviations from this table.
The pendant side groups of the branches are numbered starting from a position immediately adjacent to ring (1), where the longest chain is selected, the smaller number indicates the branch length, and the superscript number in brackets indicates the branch position, for example:
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the following table shows the illustrative structures and their corresponding abbreviations. These are presented to illustrate the meaning of the abbreviation rules. It further represents the compounds preferably used.
Table C: illustrative Structure
The following illustrative structures are examples of compounds that are preferably additionally used in the medium:
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wherein m and n are the same or different and are 1, 2, 3, 4, 5, 6 or 7.
Preferably, the medium according to the invention comprises one or more compounds selected from the compounds of table C.
Table D below shows illustrative compounds that may be used as additional stabilizers in the mesogenic media according to the invention. The total concentration of these and similar compounds in the medium is preferably 5% or less.
Table D
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In a preferred embodiment of the invention, the mesogenic media comprises one or more compounds selected from the group of compounds of table D.
The mesogenic media according to the present application preferably comprise two or more, preferably four or more compounds selected from the group consisting of the compounds of the above table.
Preferably, the medium comprises one or more chiral dopants in a concentration in the range of more than 0% to 5%, preferably 0.01 to 4%, more preferably 0.1% to 3%, very preferably 0.2% to 2%, and in particular 0.3% to 1%.
All mixtures according to the invention are nematic. The liquid-crystalline media according to the invention preferably have a nematic phase within the preferred ranges given above. The expression "having a nematic phase" means here that on the one hand no smectic phase and crystallization is observed at the corresponding temperature at low temperatures and on the other hand no conversion from nematic to isotropic phase occurs when the nematic phase is heated at a given temperature. The clearing point is measured in a capillary tube by conventional methods at elevated temperature. The study at low temperature was performed in a flow viscometer at the corresponding temperature and checked by storage of bulk samples: the storage stability (LTS) in the mass of the medium according to the invention at a given temperature T is determined by visual inspection. 2g of medium of interest are filled into appropriately sized closed glass containers (bottles) placed in a freezer at a predetermined temperature. The bottles were checked at regular time intervals for the appearance of smectic phases or crystals. Two bottles were stored for each material and at each temperature. If the appearance of crystalline or smectic phases is observed in at least one of the two corresponding bottles, the test is terminated and the time of the last inspection before the appearance of the higher order phase is observed is recorded as the respective storage stability. The test is finally terminated after 1000 hours, i.e. an LTS value of 1000 hours means that the mixture is stable for at least 1000 hours at a given temperature.
The relative tuning or relative contrast for the electro-optical response varies from 0% to 90% (t) 90 –t 0 ) The response time is determined by the rise time (τ on ) Is given, i.e. comprises a delay time (t 10 –t 0 ) The method comprises the steps of carrying out a first treatment on the surface of the The relative tuning or relative contrast for the electro-optic response changes from 100% back to 10% (t) 100 –t 10 ) The response time is determined by the decay time (τ off ) Given, and taken as the total response time (τ Totals to ＝τ on +τ off )。
m.p. represents melting point and T (N,I) Indicating liquid crystal material in degrees celsiusIs a clear point of (2); furthermore: k represents a crystalline solid state, S represents a smectic phase (index represents phase type), N represents a nematic state, ch represents a cholesteric phase, I represents an isotropic phase, T g Indicating the glass transition temperature. The numbers between the two symbols represent the conversion temperatures in degrees celsius.
All temperatures, such as the melting point T (C, N) or T (C, S) of the liquid crystal, the transition T (S, N) from smectic phase (S) to nematic phase (N), and the clearing point T (N, I), are given in degrees celsius. All temperature differences are given in degrees.
The master mix used to determine the optical anisotropy Δn of the individual compounds was the commercial mix ZLI-4792 (Merck KGaA). Dielectric anisotropy Δεwas measured using a commercial mixture ZLI-2857. Physical data for the compound to be investigated were obtained from the change in dielectric constant of the host mixture after addition of the compound to be investigated and extrapolation to 100% of the compound used. In general, depending on the solubility, 10% of the compound to be investigated is dissolved in the host mixture.
Unless indicated otherwise, parts or percent data represent parts or percent by weight.
Above and below:
V o represents the threshold voltage, capacitance at 20 [ V ]]，
n e Represents an extraordinary refractive index at 20℃and 589nm,
n o represents the ordinary refractive index at 20℃and 589nm,
Δn represents optical anisotropy at 20℃and 589nm,
ε ⊥ represents the dielectric permittivity perpendicular to the director at 20 c and 1kHz,
ε || represents the dielectric permittivity parallel to the director at 20 c and 1kHz,
delta epsilon represents the dielectric anisotropy at 20 ℃ and 1kHz,
cl.p., T (N, I) represents a clear light spot [. Degree.C ],
γ 1 represents the rotational viscosity [ mPa.s ] measured at 20 DEG C]，
K 1 Represents the elastic constant, the "splay" deformation at 20℃pN]，
K 2 Represents the elastic constant, the "distortion" deformation at 20℃pN]，
K 3 Represents the elastic constant, the "bending" deformation at 20℃pN]And (2) and
LTS means the low temperature stability (nematic phase) as measured in the test cell or body as specified.
The term "threshold voltage" as used in the present invention relates to the capacitance threshold (V 0 ) Also known as Freedericksz threshold. In an embodiment, the optical threshold (V) may also be indicated for 10% relative contrast in the usual case 10 )。
The display for measuring the capacitance threshold voltage consists of two plane-parallel glass outer plates with a spacing of 20 μm, each with an electrode layer on the inside and an unworked polyimide alignment layer on top, achieving vertical edge alignment of the liquid crystal molecules.
The display or test cell for measuring tilt angle consists of two plane parallel glass outer plates with a pitch of 4 μm, each with an electrode layer on the inside and a polyimide alignment layer on top, where the two polyimide layers rub against each other antiparallel and achieve vertical edge alignment of the liquid crystal molecules.
Tilt angle was determined using a miller matrix polarimeter (Mueller Matrix Polarimeter) "AxoScan" from Axometrics. Here, a low value (i.e., a large deviation from the 90 ° angle) corresponds to a large inclination.
Unless otherwise indicated, the term "tilt angle" means the angle between the LC director and the substrate, and "LC director" means the preferred orientation direction of the optical principal axes of LC molecules in a layer of LC molecules having uniform orientation, corresponding to their molecular long axes in the case of rod-like, uniaxially positive birefringent LC molecules.
Unless indicated otherwise, at 20 ℃ (VHR 20 ) And after 5 minutes in an oven at 100deg.C (VHR 100 ) VHR was measured in a commercially available instrument model LCM-1 (O0004) from TOYO Corporation, japan. Unless more preciselyThe frequency of the voltage used is otherwise indicated to be in the range of 1Hz to 60 Hz.
Stability to UV irradiation was studied in a commercially available instrument "Suntest cps+" from Heraeus, germany using a xenon lamp NXE 1500B. Unless explicitly indicated, the sealed test cartridge was irradiated for 2.0 hours without additional heating. An irradiation power of 765W/m in a wavelength range of 300nm to 800nm 2 V is provided. A UV "dielectric" filter with an edge wavelength of 310nm is used in order to simulate the so-called glazing mode. In each series of experiments, at least four test cassettes were studied for each condition, and the respective results are indicated as averages corresponding to the individual measurements.
The reduction in voltage holding ratio (avhr), typically caused by exposure, e.g. by UV irradiation or by LCD backlighting, is determined according to the following equation (1):
△VHR(t)＝VHR(t)-VHR(t＝0) (1)。
ion density was measured using a commercially available LC material characterization measurement system model 6254 from Toyo Corporation, japan, using a VHR test cartridge with an AL16301 polyimide (JSR corp., japan) cell gap of 3.2 μm, from which resistivity was calculated. Measurements were made after storage in an oven at 60 ℃ or 100 ℃ for 5 minutes.
The so-called "HTP" means the helical twisting power (in μm) of an optically active or chiral substance in an LC medium. HTP was measured in a commercially available nematic LC host mixture MLD-6260 (Merck KGaA) at a temperature of 20℃unless otherwise indicated.
The clearing point was measured using Mettler Thermosystem FP900,900. The optical anisotropy (. DELTA.n) was measured using Abbe-Refraktometer H005 (sodium spectrum lamp Na10 at 589nm,20 ℃). Dielectric anisotropy (. DELTA.. Epsilon.) was measured at 20℃using LCR-Meter E4980A/Agilent (G005) (epsilon. Parallel box with JALS 2096-R1). Switching voltage (V) 0 ) Is measured at 20℃using LCR-Meter E4980A/Agilent (G005) (epsilon parallel box with JALS 2096-R1). Rotational viscosity (. Gamma.) 1 ) Is carried out at 20deg.C using TOYO LCM-2 (0002) (gamma with JALS-2096-R1) 1 Negative box) to measure. Spring constant (K) 1 Splay) is performed at 20℃using LCR-Meter E4980A/Agilent (G005) (epsilon parallel box with JALS 2096-R1). K (K) 3 : spring constant (K) 3 Bending) was measured at 20℃using LCR-Meter E4980A/Agilent (G005) (epsilon parallel box with JALS 2096-R1).
All concentrations in this application are indicated in weight percent, unless explicitly stated otherwise, and refer to the entire corresponding mixture (without solvent) containing all solid or liquid crystal components. All physical properties were determined according to "Merck Liquid Crystals, physical Properties of Liquid Crystals", status 1997, month 11, merck KGaA, germany, and applicable to temperatures of 20 ℃, unless explicitly indicated otherwise.
As described in Penirschke et al, "Cavity Perturbation Method for Characterization of Liquid Crystals up to GHz",34th European Microwave Conference-Amsterdam, pages 545-548, the properties of liquid crystal media in the microwave frequency range were investigated. In this connection, A.Gaebler et al, "Direct Simulation of Material Permittivities …",12MTC 2009-International Instrumentation and Measurement Technology Conference, singapore,2009 (IEEE), pages 463-467 and DE 10 2004 029 429A are also compared, wherein the measurement method is likewise described in detail.
Liquid crystals are introduced into Polytetrafluoroethylene (PTFE) or quartz capillaries. The capillary tube has an inner diameter of 0.5mm and an outer diameter of 0.78 mm. The effective length is 2.0cm. At a resonance frequency of 19GHz, a filled capillary was introduced into the center of the cylindrical cavity. The cavity length is 11.5mm and the radius is 6mm. The input signal (source) was then applied and the reaction-dependent frequency of the cavity was recorded using a commercial vector network analyzer (N5227A PNA Microwave Network Analyzer, keysight Technologies inc. For other frequencies, the cavity dimensions are adapted accordingly.
With the aid of equations 10 and 11 described in the above-mentioned publication a.penirschke et al, 34th European Microwave Conference-Amsterdam, pages 545-548, the change in resonance frequency and Q factor between using liquid crystal filled capillary measurements and not liquid crystal filled capillary measurements was used to determine the dielectric constant and loss angle at the corresponding target frequency.
Values of characteristic components of directors perpendicular and parallel to the liquid crystal are obtained by alignment of the liquid crystal in the magnetic field. For this purpose, the magnetic field of a permanent magnet is used. The magnetic field strength was 0.35 tesla.
Dielectric anisotropy in the microwave range is defined as
Δε r ≡(ε r,|| -ε r,⊥ )。
Tunability (τ) is defined as
τ≡(Δε r /ε r,|| )。
The material quality (η) is defined as
η≡(τ/tanδ εr,max. ) Wherein
Maximum dielectric loss of tan delta εr,max. ≡max.{tanδ εr,⊥ ；tanδ εr,|| }。
Examples
The following examples are intended to illustrate the invention without limiting it. Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. Accordingly, the foregoing preferred specific embodiments are to be construed as illustrative only and not limiting of the remainder of the invention in any way whatsoever. The following examples may be repeated with similar success by substituting the reactants and/or operating conditions used in the following examples with those generally or specifically described herein. From the foregoing description, one skilled in the art can readily ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various uses and conditions.
Mixture example M1
Mixture example M2
Mixture example M3
Medium M3 consisted of 99.9% of medium M1 and 0.1% of compound S2-1 a-1.
Mixture example M4
Medium M4 consisted of 99.99% of medium M1 and 0.01% of compound S2-2 a-1.
Mixture example M5
Medium M5 consisted of 99.9% of medium M2 and 0.1% of compound S2-1 a-1.
Mixture example M6
Medium M4 consists of 99.99% of medium M2 and 0.01% of compound S2-2 a-1.
Using a peak wavelength of 460nm and irradiance of 280mW/cm 2 For blue light of (1)The LED Cube 100IC was tested for light stability. The mixture was irradiated in an ITO cell coated with polyimide (AL 3046 (CT 19320)) with a cell gap of 6 μm and VHR was measured every 2 hours at a temperature of 60 ℃ and a frequency of 60 Hz. The results are shown in table 1.
Table 1: VHR [% ] (60 ℃,60Hz, 1V)
| Mixture of | t＝0h | t＝2h | t＝4h | t＝6h | t＝8h | t＝10h | t＝12h |
| M1 | 99.3 | 94.7 | 91.2 | 88.0 | 87.3 | 87.4 | 86.7 |
| M2 | 99.1 | 95.0 | 91.7 | 89.4 | 87.2 | 86.6 | 86.3 |
| M3 | 99.6 | 99.2 | 98.7 | 98.3 | 97.9 | 97.6 | 97.3 |
| M4 | 99.3 | 92.0 | 89.7 | 91.4 | 91.8 | 90.3 | 87.3 |
| M5 | 99.6 | 99.3 | 98.8 | 97.9 | 97.0 | 96.6 | 95.9 |
| M6 | 99.1 | 93.2 | 89.9 | 92.7 | 91.0 | 88.6 | 88.3 |
Mixtures M1 to M6 have very preferred stability under blue light irradiation. The VHR value is high enough for applications in electronic devices.
Mixture example M7 contains Compound S3-3a
Mixture example M7
The medium M7 has characteristics advantageous for high frequency applications due to low dielectric loss and high tunability.
Claims (18)
1. A liquid-crystalline medium comprising
a) One or more compounds of formula I
Wherein the method comprises the steps of
R 11 R is R 12 Identically or differently represents H, alkyl or alkoxy having 1 to 12C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12C atoms, where one or more CH 2 The radicals can beInstead, and wherein one or more H atoms may be replaced by fluorine,
L 11 、L 12 、L 13 represent H, CH identically or differently 3 Cl or F,
A 11 represents phenylene-1, 4-diyl, wherein one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Replacement; cyclohexane-1, 4-diyl or cyclohexene-1, 4-diyl, wherein one or two non-adjacent CH 2 Groups may be replaced independently of one another by O and/or S and one or more H atoms may be replaced byF, replacing; bicyclo [1.1.1]Pentane-1, 3-diyl; bicyclo [2.2.2]Octane-1, 4-diyl; spiro [3.3]Heptane-2, 6-diyl; tetrahydropyran-2, 5-diyl; or 1, 3-dioxane-2, 5-diyl,
A 12 represents phenylene-1, 4-diyl, wherein one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Alternatively, or in addition, to cyclohexane-1, 4-diyl or cyclohexene-1, 4-diyl, in which one or two are not adjacent CH 2 Groups may be replaced independently of one another by O and/or S and one or more H atoms may be replaced by F,
Z 1 Represents a single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-COO-、-OCO-、-C 2 F 4 -, -cf=cf-, or-ch=chch 2 O-，
n is 0 or 1;
a kind of electronic device with high-pressure air-conditioning system
b) One or more compounds of the formula T,
wherein the method comprises the steps of
R 1 R is R 2 Represent H, F, cl, br, -CN, -SCN, -NCS, SF 5 Or a linear or branched alkyl group having 1 to 12C atoms, wherein one or more non-adjacent CH 2 The radicals can be such that the O atoms are not directly bonded to one another in each case independently of one another via-CH=CH-, -C.ident.C-, -O-, -CO-O-, -O-CO-or-O-CO-O-substitution, and wherein one or more H atoms may be replaced by F, cl or Br,
A T1 、A T2 a is a T3 Each independently of the others represents phenylene-1, 4-diyl, wherein one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 、CHF 2 、CH 2 F、CF 3 、OCH 3 、OCHF 2 Or OCF (optical clear) 3 Alternatively, wherein
A T1 Alternatively represents cyclohexane-1, 4-diyl, wherein one or two non-adjacent CH 2 Groups may be replaced independently of one another by O and/or S and one or more H atoms may be replaced by F; cyclohexene-1, 4-diyl; bicyclo [1.1.1]Pentane-1, 3-diyl; bicyclo [2.2.2]Octane-1, 4-diyl; spiro [3.3]Heptane-2, 6-diyl; tetrahydropyran-2, 5-diyl; or 1, 3-dioxane-2, 5-diyl,
Z 1 z is as follows 2 Each independently of the other represents-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、-O-CO-、-C 2 H 4 -、-C 2 F 4 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CFHCFH-、-CFHCH 2 -、-CH 2 CFH-、-CF 2 CFH-、-CFHCF 2 -, -CH=CH-, -CF=CH-, -CH=CF-, cf=cf-, -c≡c-, or a single bond,
t is 0 or 1, and the number of the T is not limited,
a kind of electronic device with high-pressure air-conditioning system
c) One or more compounds of formula S1
Wherein the method comprises the steps of
R S1 R is R S2 Represents, identically or differently on each occurrence, H or a straight-chain alkyl radical having from 1 to 25 carbon atoms or a branched alkyl radical having from 3 to 25 carbon atoms, which is unsubstituted or is substituted by CN or CF 3 Monosubstituted or at least monosubstituted by halogen, and wherein one or more CH' s 2 The radicals may each be independently of one another in such a way that the O and/or S atoms are not directly bonded to one another -O-, -S-, -CO-O-, -O-CO-O-, -ch=ch-, or-c≡C-substituted, or halogen, aryl, heteroaryl, alkylaryl or arylalkyl having 6, 5, 7 or 7 to 25 carbon atoms, respectively, each of which is unsubstituted or monosubstituted or polysubstituted by alkyl or halogen having 1 to 6C atoms,
s is 0, 1 or 2, and
t is 0, 1, 2 or 3.
2. A liquid-crystalline medium according to claim 1, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae S2 and S3
Wherein the method comprises the steps of
q is 1, 2, 3 or 4,
g represents a hydrocarbon group having 1 to 60 carbon atoms, which may be straight-chain or branched or cyclic, and which is unsubstituted or substituted by CN or CF 3 Monosubstituted or at least monosubstituted by halogen, and wherein one or more CH' s 2 The radicals may be such that O or S atoms are not directly bonded to one another and are each independently of one another via-O-, -S-, -NR 0 -, -CO-O-; -O-CO- -O-CO-O-, -CH=CH-or-C≡C-substitution,
R 0 represents H or an alkyl group having 1 to 6C atoms,
R 2 represents H, -O, -OH, a straight-chain alkyl or alkoxy group having 1 to 12C atoms or a branched or cyclic alkyl group having 3 to 25C atoms or an arylalkoxy group having 7 to 25C atoms,
R 21 r is R 22 Identically or differently represents a straight-chain alkyl radical having 1 to 12 carbon atoms or a branched alkyl radical having 3 to 12 carbon atoms, or R 21 R is R 22 Together with the carbon atoms to which it is attached form cycloalkyl groups having 5 to 12 carbon atoms,
R 23 r is R 24 Identically or differently represents a straight-chain alkyl radical having 1 to 12 carbon atoms or a branched alkyl radical having 3 to 12 carbon atoms, or R 23 R is R 24 Together with the carbon atoms to which it is attachedThe sub-groups form cycloalkyl groups having 5 to 12 carbon atoms,
Z 2 represents, identically or differently, at each occurrence, -O- >, -C (O) O-, -OC (O) -or a single bond,
R ST represents H, alkyl or alkoxy having 1 to 12C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12C atoms, where one or more CH 2 The radicals can beInstead, and wherein one or more H atoms may be replaced by fluorine,
Z ST each independently of the other represents-CO-O-; -O-CO-, -CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CH 2 -、-CH 2 CH 2 、-(CH 2 ) 4 -、-CH＝CH-CH 2 O-、-C 2 F 4 -、-CH 2 CF 2 -、-CF 2 CH 2 -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C.ident.C-or a single bond,
Which on each occurrence, are identical or different and represent cyclohexane-1, 4-diyl, cyclohexene-1, 4-diyl, pyran-2, 5-diyl or 1, 3-dioxane-2-5-diyl, wherein one or more H atoms may be replaced by F,
p is 0, 1 or 2.
3. A liquid-crystalline medium according to claim 1 or 2, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae S2-1 and S2-2
Wherein G represents a divalent aliphatic group having 1 to 20C atoms or a cycloaliphatic group having 3 to 20C atoms.
4. A liquid-crystalline medium according to one or more of claims 1 to 3, wherein the medium comprises one or more compounds selected from the group of compounds of formulae PT-1 to PT-3
Wherein R is 11 、R 12 、Z 1 、L 11 、L 12 L and L 13 Having the meaning given in claim 1.
5. Liquid-crystalline medium according to one or more of claims 1 to 4, wherein the medium comprises one or more compounds of the formula T selected from the group of compounds of the formulae T1 to T5
Wherein R is 1 R is R 2 Has the meaning indicated in claim 1 and L 2 To L 6 And represents H or F.
6. Liquid-crystalline medium according to one or more of claims 1 to 5, wherein the medium comprises one or more compounds of the formula S1-1
Wherein the method comprises the steps of
R S1 Represents H, F or Cl, and
R 21 r is R 22 Same or different represents H or a straight-chain or branched alkyl radical having 1 to 12 carbon atoms, in which one or more CH 2 The radicals may be each independently of the other so that the O atoms are not directly bonded to one another-O-, -CO-O-, -O-CO-, -ch=ch-, or-c≡c-, or aryl or aralkyl having 6 to 25 carbon atoms.
7. Liquid-crystalline medium according to one or more of claims 1 to 6, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulae II and III:
wherein the method comprises the steps of
R 2 R is R 3 Represents unsubstituted or halogenated, straight-chain or branched alkyl or alkoxy having 1 to 15C atoms, wherein one or more CH of these groups 2 The radicals being such that the O atoms are not directly bonded to one another and are each independently of one another -C≡C-、-CF 2 O-, -CH=CH-, -O-, -CO-O-, or-O-CO-, substitution,
to->Is->To->The same or different expressions
L 21 、L 22 、L 31 L and L 32 Identically or differently, H or F, preferably F,
Y 2 y and Y 3 Identically or differently represent H or CH 3 ，
X 2 X is X 3 Same or different represents halogen, halogenated alkyl or alkoxy having 1 to 3C atoms or halogenated alkenyl or alkenyloxy having 2 or 3C atoms,
Z 3 represents-CH 2 CH 2 -、-CF 2 CF 2 -, -COO-, trans-ch=ch-, trans-cf=cf-, -CH 2 O-or a single bond,
l, m, n and o are each independently 0 or 1.
8. The medium according to one or more of claims 1 to 7, wherein the medium comprises one or more compounds of formula IV
Wherein the method comprises the steps of
R 41 Represents a linear alkyl group having 1 to 12C atoms or a branched or cyclic alkyl group having 3 to 12C atoms, or a linear alkenyl group having 2 to 12C atoms or a branched alkenyl group having 3 to 12C atoms or a cyclic alkenyl group having 5 to 12C atoms, wherein one or more H atoms are optionally replaced by fluorine,
R 42 represents a linear alkyl or alkoxy radical having 1 to 12C atoms orBranched or cyclic alkyl or alkoxy groups having 3 to 12C atoms, or straight chain alkenyl groups having 2 to 12C atoms or branched alkenyl groups having 3 to 12C atoms or cyclic alkenyl groups having 5 to 12C atoms, wherein one or more H atoms are optionally replaced by fluorine.
9. The medium according to one or more of claims 1 to 8, wherein the medium comprises one or more compounds selected from the group of compounds of formulae IVa and IVb
Wherein the method comprises the steps of
R 41 R is R 42 Has the meanings defined in claim 8 independently of one another, andrepresentation of
Z 4 Represents a single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-COO-、-OCO-、-C 2 F 4 -、-C 4 H 8 -or-cf=cf-.
10. An electronic component comprising a first substrate and a second substrate facing each other, a liquid crystal medium sandwiched between the first substrate and the second substrate, electrodes provided on each substrate or two electrodes provided on only one of the substrates for providing an electric potential across the liquid crystal medium for driving a liquid crystal of a predetermined configuration, characterized in that the liquid crystal medium comprises a liquid crystal medium according to one or more of claims 1 to 9.
11. The electronic component according to claim 10, wherein the liquid crystal medium in the component is configured as a tunable dielectric configured for use in high frequency technology.
12. The electronic component according to claim 10 or 11, wherein the component is a liquid crystal based antenna component, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network or a varactor diode.
13. A microwave antenna array, characterized in that it comprises one or more components according to one or more of claims 10 to 12.
14. The assembly according to claim 10, wherein the assembly is an optical assembly operable in the visible or infrared range of the electromagnetic spectrum.
15. The component according to claim 14, wherein the component is a transmissive spatial light modulator.
16. The component of claim 14, wherein the component is a reflective spatial light modulator (100) configured to modulate a phase of an incident optical signal propagating at least partially in a first dimension, wherein the first substrate is a transparent glass layer (110) having a first transparent electrode (120), and wherein the second substrate is a CMOS silicon backplane (160), the component further comprising a mirror (150) disposed between the second substrate and a liquid crystal medium (140), wherein the mirror is divided into a two-dimensional array of individually addressable pixels arranged and configured as a second electrode (150), each pixel being individually drivable by a voltage signal to provide a local phase change to at least one polarization component of the optical signal.
17. An optical device, comprising:
RGB light source
The component according to one or more of claims 14 to 16, arranged and configured to modulate the phase of an incident optical signal from the RGB light sources when operating an optical device.
18. A method of spatially modulating light, the method comprising,
i) Providing an optical component comprising first and second substrates facing each other and each having a surface, the first substrate comprising at least one first electrode and the second substrate comprising at least one second electrode, the component further comprising a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises a liquid crystal medium according to one or more of claims 1 to 9;
ii) providing an RGB light source;
ii) receiving incident light from the RGB light sources at a surface of the optical assembly;
iii) A predetermined voltage is applied to each of the individual electrodes formed on the first substrate so as to modulate the refractive index of the liquid crystal layer.
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